Methods of modifying a naturally occurring cannabis raw plant material, a purified cannabis product from a naturally occurring cannabis raw plant material, and a modified cannabis product from a naturally occurring cannabis raw plant material

ABSTRACT

A method of modifying a naturally occurring Cannabis raw plant material, a purified Cannabis product from a naturally occurring Cannabis raw plant material, and a modified Cannabis product from a naturally occurring Cannabis raw plant material. The method includes selectively extracting at least some volatile organic compounds from a naturally occurring Cannabis raw plant material. At least some of a naturally occurring potential cannabinoid content in the Cannabis raw plant material is retained after removal of the at least some of the volatile organic compounds as well as substantially all of the physical structure of the Cannabis raw plant material.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a Continuation-in-Part of application Ser. No. 17/098,539, filed Nov. 16, 2020, which is a Continuation of application Ser. No. 16/912,031, filed Jun. 25, 2020 (now U.S. Pat. No. 10,835,839), which is a Continuation of application Ser. No. 16/255,157, filed Jan. 23, 2019 (now U.S. Pat. No. 10,737,198), which claims priority to Provisional Application No. 62/620,726, filed Jan. 23, 2018, and Provisional Application No. 62/633,478, filed Feb. 21, 2018. The contents of the prior applications are hereby incorporated by reference in their entireties.

TECHNICAL FIELD

This application relates to methods for purifying and modifying a Cannabis product by removing volatile organic compounds and/or essential oils to produce a new and unique Cannabis product and optionally further adding volatile organic compounds to the Cannabis product to produce a modified Cannabis product for recreational and medicinal use, including use in the food and beverage industries.

BACKGROUND

Cannabis is a genus of flowering plants in the family of Cannabaceae and includes at least three known species: Cannabis sativa, Cannabis indica and Cannabis ruderalis. Marijuana and Hemp are forms of Cannabis. Marijuana includes all varieties of the Cannabis genus that contain substantial amounts of THC and is conventionally used for recreational or medicinal purposes. Hemp includes all varieties of the Cannabis genus that contain negligible amounts of THC and generally refers to the industrial, non-drug variant of Cannabis that is cultivated for its flower leaf material, fiber, hurd, and seeds. Hemp flower is used in the production of CBD oils, ointments and extracts used in various dietary supplements as well as the production of Hemp cigarettes that contain CBD compounds. The Hemp seed is mainly used in dietary products and can also be pressed and made into oil that can be used as salad dressing, paint, ink, and as a core ingredient in many body care products. The Hemp stalk and its fiber have more than 25,000 industrial uses, including mainly clothing, construction materials, paper, apparel, bags, rope, netting, canvas, and carpet. Hemp hurds can be used in cement, insulation, paper, animal bedding, biodegradable garden mulch, and plastics.

Through selective breeding or genetic modification, several varieties or strains of Cannabis have been produced, all of which are considered Cannabis. Cannabis is used as a drug or medicine for medicinal and recreation uses. It is consumed through smoking (combustion and inhalation) Cannabis plant material, plant extracts or purified or modified compounds, or through ingestion of the plant material, plant extracts or purified or modified compounds. The most commonly recognized biologically active components of Cannabis include Δ9-tetrahydrocannabinol (THC) and cannabidiol (CBD). At least 483 known compounds are found in Cannabis including at least 113 other cannabinoids which may have a yet unidentified medicinal benefit.

Cannabis can be used by smoking the dried plant material, by smoking of extracts of the plant material, or by orally consuming with food, or by consuming as an extract. To date, thirty-six States, the District of Columbia, the US. Virgin Islands, Guam and Puerto Rico have passed laws allowing Cannabis to be used for a variety of medical conditions. Currently, nineteen states, two U.S. territories and the District of Columbia have adopted laws legalizing Cannabis for recreational use. The non-medical use of Cannabis has been decriminalized in twenty-nine States. In addition, Canada has legalized both medicinal and recreational Cannabis in all provinces as of Oct. 17, 2018, and Canada legalized the growing and use of Hemp for any and all commercial purposes as of May of 1998.

As of Dec. 20, 2018, with the enactment of the 2018 Farm Bill, Hemp, which is defined in the Bill as the plant Cannabis sativa L. and any part of that plant, including the seeds thereof and all derivatives, extracts, cannabinoids, isomers, acids, salts, and salts of isomers, whether growing or not, with a THC concentration of not more than 0.3 percent on a dry weight basis, has become legal in all fifty states and is no longer considered a controlled substance subject to regulation by the United States Drug Enforcement Agency.

Cannabis has a distinct strong and pungent odor, primarily as a result of several volatile small molecules including, but not limited to, terpenes and thiols, and collectively described as volatile organic compounds and/or essential oils.

Terpenes are ubiquitous throughout the plant world and are produced by a myriad of plant species. Terpenes are commonly found in fruits, vegetables, herbs, spices, and other botanicals. They are also common ingredients in the human diet and have generally been recognized as safe to consume by the United States Food and Drug Administration. The general class of molecules that encompass terpenes can be further broken down into mono-terpenes, diterpenes and sesquiterpenes, sesterterpenes, triterpenes, sesquarterpenes, tetraterpenes, polyterpenes, and norisoprenoids, contingent on the number of repeating units of a five-carbon molecule referred to as isoprene which is the structural hallmark of all terpenoid compounds. The term terpenoid is used to describe a derivative of a terpene. Terpenes are among the volatile organic compounds found in the essential oils of many types of plants and flowers. Essential oils are used widely as fragrances in perfumery and in medicine and alternative medicines such as aromatherapy. Synthetic variations and derivatives of natural terpenes (terpenoids) greatly expand the possible numbers of potential terpenoids which could be used to modify the flavor and aroma of Cannabis.

Although terpenes may possess some medical benefits, the flavor and smell that results from the presence of these terpenes may be found undesirable by many users of Cannabis. Moreover, the strong and pungent odor can linger for hours in the environment, as well as in the clothing of the individuals present during smoking. Because the odor is distinct and easily recognizable as that of Cannabis, it is difficult to smoke Cannabis with discretion, which presents a limitation on their use. Since Cannabis-based products may be used for medicinal purposes, the removal of this strong and pungent odor is especially desirable.

Thiols, also known as mercaptans, are sulfur-containing organic compounds with a sulfur atom bound to a hydrogen atom, i.e., an —SH functional group. The —SH functional group is the sulfur analog of a hydroxyl or alcohol group. The functional group is referred to as either a thiol group or a sulfhydryl group. Thiols and alcohols have similar molecular structure, although the C—S—H bond angle is closer to 90° than the C—O—H bond angle of alcohol. In the solid or liquid state, the hydrogen bonding between individual thiol groups is weak, the main cohesive force being van der Waals interactions between the polar sulfur centers. Thiols present challenges in the food, beverage and Cannabis industries because of their low concentration and high reactivity, which results in difficulty in analysis and management. Moreover, measurement and management apparatuses are very expensive, and few laboratories have the necessary equipment to perform an adequate analysis. Thiols also have a strong and pungent odor and have been said to contribute to the unpleasant small of Cannabis in several recent studies.

Some processes for the extraction of Cannabis compounds are known. While conventional compound extraction processes are generally known, these processes remain inefficient and cost-ineffective due to the number of variables. None of the conventional processes contemplate selectively extracting a volatile organic compound such as an essential oil, including terpenes and/or thiols, (natural or synthetic) from a Cannabis raw plant material to form a purified Cannabis product, where the purified Cannabis product retains the desired naturally occurring Total Potential cannabinoid content (i.e., an amount of naturally occurring cannabinoid plus any decarboxylated cannabinoid acids) in the Cannabis raw material after the extraction.

Additionally, the resulting products tend to exhibit reduced efficacy and/or substandard odor and flavor due to the “wholesale” removal of desired ingredients along with the compound targeted for removal. In this regard, it is not conventionally known to selectively extract terpenes and/or thiols while retaining substantially all of the Total Potential cannabinoid content, or to further modify a previously-modified Cannabis product, where the previously-modified or purified Cannabis product is substantially free of a target compound or compounds that detracts from a desired user experience. Further, current methods to isolate the potential cannabinoids, commonly called “extractions” result in the significant loss of the terpenes and/or the thiols as well as the plant structure itself.

Accordingly, there is a need for a comprehensive and cohesive approach to process Cannabis to provide a low, or no, odor and/or reduced or modified flavor form of Cannabis, with minimal loss of plant structure. In this regard, if the volatile organic compounds such as essential oils, including terpenes and/or thiols, (natural or synthetic) were to be removed without affecting the Total Potential cannabinoid content, the Cannabis could be used without leaving a strong and obvious odor on the user or subjecting the user to what may be deemed to be an unpleasant taste. These and other advantages are exhibited by the following disclosed embodiments.

SUMMARY

Disclosed embodiments provide purified and modified Cannabis products without the above-described drawbacks in order to create a more desirable experience for the user in terms of the odor and flavor of the inhaled product, while at the same time preserving the naturally occurring Total Potential cannabinoid content thereof and leaving both the purified and the modified Cannabis raw plant material undamaged and still in a condition that it can be smoked in the same manner as before it was modified.

To this end, the disclosed embodiments are directed to novel Cannabis products that do not produce the characteristic odor and flavor typically associated with the smoking (combustion and subsequent inhalation) of unmodified Cannabis plant material and methods of removing or significantly reducing the volatile organic compounds from Cannabis raw plant material (“primary modification”). Further, new and novel Cannabis products are then provided that have new and unique odors and flavors that exist as modified Cannabis products by methods of further modifying the primarily modified Cannabis products by adding volatile organic compounds, such as volatile unsaturated hydrocarbons, either naturally occurring or synthetically produced, including, but not limited to, essential oils, flavorings or terpenes (natural or synthetic) (“secondary modification”).

In a first embodiment, there is provided a method of modifying a naturally occurring Cannabis raw plant material. The method includes selectively extracting at least some volatile organic compounds from a naturally occurring Cannabis raw plant material. At least some of a naturally occurring potential cannabinoid content in the Cannabis raw plant material is retained after removal of the at least some of the volatile organic compounds.

In another embodiment, there is provided a purified Cannabis product from a naturally occurring Cannabis raw plant material. The purified Cannabis product comprises cannabinoids, and a reduced amount of volatile organic compounds relative to the Cannabis raw plant material. At least one thiol compound has been removed from the Cannabis raw plant material to form the purified Cannabis product, and at least some of a naturally occurring potential cannabinoid content in the Cannabis raw plant material is retained in the purified Cannabis product after removal of the at least one thiol compound.

In another embodiment, there is provided a modified Cannabis product from a naturally occurring Cannabis raw plant material. The modified Cannabis product comprises cannabinoids, and at least one volatile organic compound. At least some volatile organic compounds have been removed from the Cannabis raw plant material to form a purified Cannabis product, at least one volatile organic compound has been added to the purified Cannabis product to form the modified Cannabis product, and at least some of a naturally occurring cannabinoid content of the Cannabis raw plant material is retained in the purified Cannabis product after removal of the at least one thiol compound.

In another embodiment, there is provided a method of extracting at least some volatile organic compounds from a naturally occurring Cannabis raw plant material. The method comprises adjusting a pressure of a variable-pressure steam extraction apparatus based on a boiling point of at least one volatile organic compound in the naturally occurring Cannabis raw plant material, and selectively extracting the at least some volatile organic compounds from the naturally occurring Cannabis raw plant material in the variable-pressure steam extraction apparatus by operating the variable-pressure steam extraction apparatus at the pressure.

BRIEF DESCRIPTION OF THE DRAWINGS

The disclosed embodiments will now be described with reference to the following figures.

FIG. 1 illustrates a steam extraction system that can be used for primary modification of Cannabis raw plant material according to an embodiment.

FIG. 2 illustrates a flow chart of a steam extraction process that can be used for primary modification of Cannabis raw plant material according to an embodiment.

FIG. 3 illustrates a vacuum desiccation system that can be used for primary modification of Cannabis raw plant material according to an embodiment.

FIG. 4 illustrates a flow chart of a secondary modification process of primarily modified Cannabis raw plant material according to an embodiment.

FIGS. 5A-5F illustrate analytical results of Marijuana samples according to embodiments.

FIGS. 6A-6F illustrate analytical results of Hemp samples according to embodiments.

FIG. 7 illustrates a variable-pressure steam extraction system that can be used for primary modification of Cannabis raw plant material according to an embodiment.

FIG. 8 illustrates a flow chart of a variable-pressure steam extraction process that can be used for primary modification of Cannabis raw plant material according to an embodiment.

FIGS. 9A and 9B illustrate analytical results of a Hemp sample processed using a variable-pressure steam extraction system according to an embodiment.

FIGS. 10A and 10B illustrate analytical results of a Hemp sample processed using a variable-pressure steam extraction system according to an embodiment.

FIGS. 11A and 11B illustrate analytical results of a Hemp sample processed using a variable-pressure steam extraction system according to an embodiment.

FIGS. 12A and 12B illustrate analytical results of a Hemp sample processed using a variable-pressure steam extraction system according to an embodiment.

FIGS. 13A and 13B illustrate analytical results of a Hemp sample processed using a variable-pressure steam extraction system according to an embodiment.

FIGS. 14A and 14B illustrate analytical results of a Hemp sample processed using a variable-pressure steam extraction system according to an embodiment.

FIGS. 15A and 15B illustrate analytical results of a Hemp sample processed using a variable-pressure steam extraction system according to an embodiment.

FIGS. 16A and 16 illustrate analytical results of a Hemp sample processed using a variable-pressure steam extraction system according to an embodiment.

FIGS. 17A and 17B illustrate analytical results of a Hemp sample processed using a variable-pressure steam extraction system according to an embodiment.

FIGS. 18A and 18B illustrate analytical results of a Hemp sample processed using a variable-pressure steam extraction system according to an embodiment.

FIGS. 19A and 19B illustrate analytical results of a Hemp sample processed using a variable-pressure steam extraction system according to an embodiment.

FIGS. 20A and 20B illustrate analytical results of a Hemp sample processed using a variable-pressure steam extraction system according to an embodiment.

FIGS. 21A and 21B illustrate analytical results of a Hemp sample processed using a variable-pressure steam extraction system according to an embodiment.

FIGS. 22A and 22B illustrate analytical results of a Hemp sample processed using a variable-pressure steam extraction system according to an embodiment.

FIGS. 23A and 23B illustrate analytical results of a Hemp sample processed using a variable-pressure steam extraction system according to an embodiment.

FIGS. 24A and 24B illustrate analytical results of a Hemp sample processed using a variable-pressure steam extraction system according to an embodiment.

DETAILED DESCRIPTION

As used herein, Cannabis includes any plant or plant material derived from a Cannabis plant (i.e., Cannabis sativa, Cannabis indica and Cannabis ruderalis), naturally or through selective breeding or genetic engineering. The Cannabis may be used for therapeutic, medicinal, research, recreational purposes or any yet unforeseen purpose. Ways for consuming Cannabis according to embodiments may include, but are not limited to, inhalation by smoking dried Cannabis plant material, inhalation by smoking Cannabis plant extracts or by ingesting Cannabis plant material or plant extracts such as, for example, in the form of edible Cannabis products that incorporate raw plant material, where potentially undesirable odor and/or taste has been removed and a possibly more desirable odor/taste has been added to the raw plant material. For purposes of this disclosure, the disclosed embodiments will be described with respect to the production of a modified form of dried Cannabis plant material for consumption by inhalation after combustion. It will be understood that the disclosed products and methods may apply to all types, forms and uses of Cannabis.

As used herein, as stated, Marijuana includes all varieties of the Cannabis genus that contain substantial amounts of THC. As used herein, Hemp includes all varieties of the Cannabis genus that contain negligible amounts of THC. Hemp specifically includes the plant Cannabis sativa L. and any part of that plant, including the seeds thereof and all derivatives, extracts, cannabinoids, isomers, acids, salts, and salts of isomers, whether growing or not, with a THC concentration defined according to relevant regulations. For example, the 2018 Farm Bill and many states define Hemp as having a THC concentration of not more than 0.3 percent on a dry weight basis. Many states have adopted similar definitions. Notably, West Virginia defines Hemp as Cannabis with a THC concentration of less than 1.0 percent. Many state definitions for industrial Hemp specify that THC concentration is on a dry weight basis and can be measured from any part of the plant. Some states also require the plant to be possessed by a licensed grower for it to be considered under the definition of industrial Hemp.

In the embodiments, there are provided purified Cannabis products comprising naturally occurring cannabinoids and substantially no volatile organic compounds and modified Cannabis products comprising naturally occurring and/or decarboxylated cannabinoids and at least one volatile organic compound. In other embodiments, there are provided methods for selectively extracting volatile organic compounds from a Cannabis raw material to form a purified Cannabis product (primary modification) and adding at least one volatile organic compound to a purified Cannabis product to form a modified Cannabis product (secondary modification).

Volatile Organic Compounds

It is commonly known that the characteristic smell and flavor of Cannabis when smoked is primarily the result of volatile organic compounds. Volatile organic compounds are organic chemical compounds whose composition makes it possible for them to evaporate under normal indoor atmospheric conditions of temperature and pressure. Volatile organic compounds include saturated hydrocarbons and unsaturated (i.e., having at least one double carbon-carbon bond) hydrocarbons.

In embodiments, volatile organic compounds include terpenes and thiols. Terpenes and thiols are primary constituents of the essential oil extracts of Cannabis. Therefore, the disclosed embodiments provide a Cannabis product that is produced by removing or reducing the naturally occurring compliment of volatile organic compounds from Cannabis, which produce the characteristic smell of Cannabis and primarily include, but are not limited to, terpenes and/or thiols, and are collectively known as the essential oils.

Terpenes

Most terpenes are volatile organic compounds including unsaturated hydrocarbons and which contain an —SH functional group. At least 200 terpenes are found in the Cannabis plant but 14 are commonly found in significant quantities, which vary in quantity depending on the strain of the Cannabis plant. The molecular structure of these common terpenes, i.e., isoprene, α-pinene, β-pinene, Δ3-carene, d-limonene, camphene, myrcene, β-phellandrene, sabinene, α-terpinene, ocimene, α-thujene, terpinolene and γ-terpinene, are shown below.

Terpenes serve as the precursors for the synthesis of chemicals used in the production of food, cosmetics, and are regularly used in the pharmaceutical and biotechnology industries. Chemical synthesis of terpenes can be challenging in light of their complex structure, and since most plants produce them is small amounts, extracting terpenes from natural plant sources is often difficult, time-consuming and cost-prohibitive. To date, the genomes of 17 plant species have been shown to contain the genes that encode terpenoid synthase enzymes imparting terpenes with their basic structure, as well as the enzyme cytochrome P450s, which is required to modify this basic structure. It is believed that all known terpenes are synthesized by the enzyme terpene synthase.

Terpenes are biosynthetically produced from units of isoprene, which has the basic molecular formula C₅H₈. The molecular formula of terpenes is a multiple of that molecular formula, (C₅H₈)^(n) where n is the number of linked isoprene residues. This is commonly referred to as the isoprene rule or sometimes the C5 rule. The isoprene units can be linked together “head to tail” to form straight chains and can also be arranged to form rings. Indeed, the isoprene unit is one of nature's most common building blocks. As chains of isoprene units are synthesized, the resulting terpenes are classified consecutively according to their size as hemiterpenes, monoterpenes, sesquiterpenes, diterpenes, sesterterpenes, triterpenes, tetraterpenes and polyterpenes.

Terpenes may be categorized by the number of isoprene units that make up the molecule. The number of terpene units that make up the molecule is designated by the prefix of the name. For example, hemiterpenes consist of a single isoprene unit. Isoprene is considered the only hemiterpene, but oxygen-containing derivatives such as prenol and isovaleric acid are hemiterpenoids.

Monoterpenes consist of two isoprene units and have the molecular formula C₁₀H₁₆. Examples of monoterpenes and monoterpenoids include geraniol, terpineol (present in lilacs), myrcene (present in hops), limonene (present in citrus fruits), linalool (present in lavender) and pinene (present in conifers).

Sesquiterpenes consist of three isoprene units and have the molecular formula C₁₅H₂₄. Examples of sesquiterpenes include humulene (also known as α-humulene or α-caryophyllene), and farnesene, which refers to a set of six closely related chemical compounds which all are sesquiterpenes (the sesqui-prefix indicates one and a half).

Diterpenes are composed of four isoprene units, which have the molecular formula C₂₀H₃₂ and are derive from geranylgeranyl pyrophosphate; an intermediate in the biosynthesis of some terpenes and terpenoids. Examples of diterpenes and diterpenoids are cafestol, kahweol, cembrene and taxadiene (precursor of taxol). Diterpenes also form the basis for biologically important compounds such as retinol, retinal, and phytol.

Sesterterpenes, which have 25 carbons and five isoprene units, are rare relative to the other terpenes (the sester-prefix means half to three, i.e., two and a half). An example of a sesterterpenoid is geranylfarnesol.

Triterpenes comprise six isoprene units and have the molecular formula C₃₀H₄₈. An example of a triterpenes is squalene, the main constituent of shark liver oil. Squalene can also be biosynthetically processed to generate lanosterol or cycloartenol, the structural precursors to all the steroids.

Sesquarterpenes are composed of seven isoprene units and have the molecular formula C₃₅H₅₆. Sesquarterpenes are typically microbial in their origin. Examples of sesquarterpenoids are ferrugicadiol and tetraprenylcurcumene.

Tetraterpenes contain eight isoprene units and have the molecular formula C₄₀H₆₄. Biologically important tetraterpenoids include the acyclic lycopene, the monocyclic gamma-carotene, and the bicyclic alpha- and beta-carotenes.

Polyterpenes consist of long chains of many isoprene units. Natural rubber consists of polyisoprene in which the double bonds are cis. Some plants produce a polyisoprene with trans double bonds, known as gutta-percha.

Norisoprenoids, such as the C13-norisoprenoids 3-oxo-α-ionol present and 7,8-dihydroionone derivatives, such as megastigmane-3,9-diol and 3-oxo-7,8-dihydro-α-ionol found in Muscat of Alexandria and Shiraz leaves, respectively (grapes in the species Vitis vinifera) are responsible for some of the spice in Chardonnay, can be produced by fungal peroxidases or glycosidases.

Isoprene itself does not directly feed into the biosynthetic pathway but rather the activated forms, isopentenyl pyrophosphate (IPP or also isopentenyl diphosphate) and dimethylallyl pyrophosphate (DMAPP or also dimethylallyl diphosphate), are the components in the biosynthetic pathway. IPP is formed from acetyl-CoA via the intermediacy of mevalonic acid in the HMG-CoA reductase pathway.

Thiols

Thiols are volatile organic compounds which include saturated or unsaturated hydrocarbons. In embodiments, the thiol may be 3-methyl-2-butene-1-thiol (“321 MBT”). The skunky-like aroma commonly associated with raw Cannabis material is due, at least in part, to 321 MBT. Other thiols include, but are not limited to, 4-mercapto-4-methylpentan-2-one (4MMP), 3-mercaptohexan-1-ol (3MH or EMH), and 3-mercaptohexyl acetate (3MHA), which are commonly found in recreational beverages, including beer and wine. The molecular structure of MBT, 4MMP, EMH, and 3MHA are shown below.

A combination of volatile organic compounds, including terpenes and different thiols or other sulfur-containing compounds (shown above), combine synergistically to yield the characteristic smell of cannabis. The presence or absence of any specific volatile organic compound, as well as differences in cannabinoids, are largely responsible for differences between different cannabis cultivars. For instance, the cultivar Bacio Gelato has significantly more 321 MBT then the varietal Black Jack, which has very little (see Oswale et al. ACS Omega 2021, 6, 47, 31667-31676). Therefore, the starting material can be selectively chosen to allow extraction process to be at a lower temperature, whereas varietals with other volatiles, typically of higher molecular weight, may require extractions at higher temperatures. These include temperatures higher above the boiling water at sea level and may be achieved at increased pressure.

Cannabinoids

In addition to these terpenes and/or thiols, cannabinoids are also found in Cannabis. These cannabinoids do not appreciably contribute to the complement of organic molecules found in the essential oils. The molecular structure of nine cannabinoids found in Cannabis produced under elevated temperature are shown below.

Purified Cannabis Product

A purified Cannabis product according to the disclosed embodiments includes naturally occurring cannabinoids, and substantially no volatile organic compounds. The purified Cannabis product is formed by selectively extracting the volatile organic compounds from a Cannabis raw plant material to form the purified Cannabis product. Substantially all of a naturally occurring potential cannabinoid content in the raw material is retained in the purified Cannabis product after the extraction, and substantially all of a naturally occurring physical structure of the Cannabis product is retained in the purified Cannabis product after the extraction so that the purified Cannabis product can be combusted and inhaled in a manner similar to a naturally occurring Cannabis product under similar conditions.

A method (i.e., primary modification) for forming the purified Cannabis product is as follows. In the embodiments, Cannabis raw plant material is subjected to any process that removes or significantly reduces the amount of volatile organic compounds, such as essential oils, or terpenes and/or thiols, without removing a significant amount of the naturally occurring Total Potential of cannabinoids (e.g., THC and CBD), or negatively impacting the naturally occurring physical structure of the original Cannabis plant material itself. The amount of naturally occurring Total Potential cannabinoid content retained from the Cannabis depends on the desired purified product (i.e., the degree of activity based on desired user experience). In embodiments, substantially all of the Total Potential cannabinoid content may be retained. Alternatively, 5%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 99% or 99.9%, by mass %, of the Total Potential cannabinoid content may be retained. Depending on the desired purified product, the amount of Total Potential cannabinoid content retained may be in a range of 25% to 100%, 50% to 99.9%, 75% to 99%, 90% to 99%, 50% to 99%, 70% to 99.9%, 80% to 99%, or 90% to 99.9%, by mass %. Preferably, as much of the naturally occurring Total Potential cannabinoid content is retained as possible.

The amount of volatile organic compound removed from the Cannabis depends on the desired purified product (i.e., the degree of purity based on desired user or patient experience). In embodiments, substantially all of the compound may be removed. Alternatively, 5%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 99% or 99.9%, by mass %, of the compound may be removed. Depending on the desired purified product, the amount of compound removed may be in a range of 25% to 100%, 50% to 99%, 70% to 99.9% or 90% to 99.9%, by mass %.

It will be understood that the terms “remove,” “removal,” “reduce,” “reduction,” and the like, when used in the context of the disclosed processes are meant to imply the removal, reduction, or neutralization, of a significant amount of a substance or chemical but that it may not be practical for most such processes to remove or reduce 100% of a substance or a chemical. It will also be understood that the terms “retain,” “retained,” and the like, when used in the context of the disclosed processes are meant to imply the retention of a significant amount of a substance or chemical but that it may not practical for most such processes to retain 100% of a substance or a chemical. Accordingly, it will be understood that “substantial” removal/retention or “substantially” removing/retaining for the purposes of this disclosure may include a tolerance known or generally accepted in the cannabis and chemical processing industries. For example, “substantial” removal/retention or “substantially” removing/retaining may include a tolerance in a range of 0 to 5%, 0.001 to 5%, 0.01 to 5%, 0.1 to 5%, 0.001 to 1%, 0.01 to 1%, 0.1 to 1%, 0.001 to 0.1%, or 0.001 to 0.01%.

In the purified Cannabis product, the ratio of an amount of cannabinoids (e.g., THC and CBD), to the remaining amount of volatile organic compound, such as a terpene and/or a thiol, may be in the range of 100:0, 10:90, 25:75, 50:50, 60:40, 75:25, 90:10, 95:5, or 99:1, by mass %. Similarly, the ratio of an amount of the total amount of non-volatile organic compound ingredients to the remaining amount of volatile organic compound, may be in the range of 100:0, 10:90, 25:75, 50:50, 60:40, 75:25, 90:10, 95:5, or 99:1, by mass %.

Methods of producing the primarily modified Cannabis product by removing the essential oils of naturally occurring Cannabis raw plant material may include any suitable method known in the art. For example, methods of producing the primarily modified Cannabis product by removing the essential oils of naturally occurring Cannabis raw plant material may include, but are not limited to, steam extraction by passing steam over the material, including superheated steam extraction, volatizing the essential oils through reduced atmospheric pressure and/or increased temperature and/or atmospheric pressure, solvent extraction with an organic and/or non-organic liquid, a solvent of neutral pH, increased pH or reduced pH, supercritical CO2 extraction, subcritical water extraction, hydrodistillation, hydrodiffusion, submersion in an organic or non-organic solvent at room temperature or at an increased or decreased temperature, expression, absolute oil extraction, resin tapping, cold pressing, neutralization, selective breeding or genetic engineering or modification (e.g., genetically engineering without or with a defective terpene synthase gene), or any combination of the above-described methods or processes.

Knocking down or knocking out a gene to remove its ability to produce a terpene is synonymous in the context of the disclosed embodiments with extracting or removing the terpene. The concentration of terpenes is associated with naturally occurring genetic variations in the terpene synthase genes. Knocking out any one or more terpene synthase genes would have the effect of decreasing or eliminating the downstream terpene product. Therefore, modifying the terpene synthase genes has the capacity to either increase or decrease the content of terpenes in the plant. With respect to decreasing the level of terpenes produced by the plant, this may be accomplished by making the gene defective or by eliminating the gene either partially or completely.

In the embodiments, removal of volatile organic compounds, including the terpenes and/or thiols, from Cannabis may be executed by the use of a steam extraction apparatus 10 that may be used to isolate the essential oils from plants, as shown in FIG. 1. In this system, water is boiled below the Cannabis and the steam is allowed to pass through the Cannabis raw plant material. The starting material can be either dried or undried unmodified Cannabis raw plant material. The volatile organic compounds, including the terpenes and/or thiols, are volatilized by the steam and are carried with the steam into a condenser that cools the steam and volatile organic compounds where it recondenses. The condensed water and volatile organic compounds then flow into a collection flask. Cannabinoids are typically much larger (greater molecular weight) than the terpenes and/or thiols found in plants and hence are less volatile and have higher melting points because their dispersion forces increase with the larger number of atoms. Decrease in binding of outer electrons to the nucleus also increases van der Waals-type interactions of the atom due to its increased polarizability. Because cannabinoids are much less volatile than the terpenes and/or thiols, the cannabinoids are retained in the Cannabis raw plant material. The Table below illustrates the molecular weights and boiling points associated with common terpenes and cannabinoids found in Cannabis.

List of Common Terpenes and Cannabinoids Found in Cannabis Terpenes Cannabinoids* M.W. B.P. M.P. M.W. B.P. # M.P. Name (g/mol) (° C.) (° C.) Name (g/mol) (° C.) (° C.) Isoprene  68.11 34.1 −145.9 Δ9-tetrahydrocannabinol 314.46 390.4 ± 42.0 200 α-pinene 136.23 157.9 −55 Cannabinol 310.43 476.5 76-77 β-pinene 136.23 166 −61 Cannabidiol (-trans) 314.46 463.9 ± 45.0 62-63 Carene 136.23 171.4 <25 Cannabicyclol 314.46 382.1 N/A D-Limonene 136.23 175.4 −74 Cannabitriol 346.46 418   176 Camphene 136.23 157.5 35 Cannabigerol 316.48 470.4 49-52 Myrcene 136.23 167 −10 Cannabichromene 314.46 428.7 ± 45.0 N/A β-phellandrene 136.23 175 −40 Cannabielsoin 330.46 N/A N/A Sabinene 136.23 164 N/A Cannabinodiol 310.43 497.3 ± 40.0 N/A α-terpinene 136.23 174.1 −40 Tetrahydrocannabivarin 286.41 360.6 N/A Ocimene 136.23 170.2 50 Cannabidivarin 286.41 439.4 ± 45.0 N/A α-thujene 136.23 152 N/A Cannabichromevarin 286.41 401.4 ± 45.0 N/A Terpinolene 136.23 182 <25 γ-terpinene 136.23 183 60-61 *Represents the decarboxylated form of the naturally occurring acid #At 760 mmHg Values from www.chemsrc.com or http://www.chemspider.com when available

In another embodiment, removal of volatile organic compounds, including the terpenes and/or thiols, from Cannabis may be achieved by the use of a variable-pressure steam extraction apparatus that may be used to isolate the essential oils from plants. It is known that under a pressurized system, water and other liquids boil at a higher temperature, i.e., the higher the pressure, the higher the boiling point and the higher the temperature of the steam. Therefore, in embodiments, the variable-pressure steam extraction apparatus may be configured to operate under reduced pressure or increased pressure depending on the desired compounds to be extracted or selectively (i.e., selected based on boiling point) extracted.

An exemplary variable-pressure steam extraction apparatus 100 is illustrated in FIG. 7. As seen in FIG. 7, the variable-pressure steam extraction apparatus 100 includes a heat source 101. In embodiments, the heat source is not particularly limited and may be any suitable heat source including, but not limited to, an electric or gas heater. The variable-pressure steam extraction apparatus 100 may include a reservoir 102 for holding liquid 121, such as water, to be heated by the heater 101, a processing column 103 for holding a raw Cannabis plant material 123, and a condenser 104 for condensing steam 122 generated in the reservoir 102 and passed through the processing column 103, as seen in FIG. 7. A coupler 105 is provided for fluidly connecting the reservoir 102 and container 103 and allowing steam to pass therethrough, and a conduit 106 is provided for fluidly connecting the processing column 103 and condenser 104 and allowing steam, volatile organic compounds and essential oils to pass therethrough. In embodiments, the coupler 105 may include a silicon gasket and a vacuum pump clamp. The variable-pressure steam extraction apparatus 100 may include a pressure gauge 107 configured to measure a pressure in the reservoir 102, an adjustable pressure valve 108 configured to adjust pressure in the conduit 109, pressure safety release 109 for controlling a pressure in the reservoir 102, and a temperature gauge 110 for measuring a temperature in the processing column 103. The condenser 104 may include a fitting 111 for connecting to a cold water inflow stream, and fitting 112 to connect a tube to where the waste water flows from. An extract container 150 is provided for receiving water, volatile organic compounds and essential oils output from the condenser 104, as shown in FIG. 7. In embodiments, the extract container 150 may be a beaker or a separatory funnel.

In this embodiment, water is boiled under variable pressure below the Cannabis and the steam passes through the Cannabis raw plant material. In embodiments, the pressure may range from 0.0001 to 100 bar, 0.001 to 50 bar, 0.001 to 15 bar, 0.001 to 1 bar, 0.001 to 0.99 bar, or 0.01 to 0.90 bar. Accordingly, the temperature of the steam in the apparatus may range from 0° C. to 300° C., 1° C. to 250° C., or preferably, 4° C. to 200° C. Moreover, the pressure of the extraction may be standardized using increased pressure. For instance, extractions that are carried out above sea level (less than 1 atmosphere) may be standardized by increasing the pressure of the reaction system to that equal to one 1 atmosphere.

When water is boiled at different pressures, the temperature of the steam is selectively altered, and in turn, different volatile organic compounds are selectively volatilized by the steam and are carried with the steam into a condenser that cools the steam back to liquid water so that the volatile organic compounds can be extracted. Because the volatility of cannabinoids is much less than that of water, as well as the terpenes and/or thiols, the cannabinoids are retained in the Cannabis raw plant material.

Because the boiling point of the volatile organic compounds exhibit varying sensitivities to heat, volatile organic compounds are selectively volatilized by the steam and are carried with the steam into a condenser that cools the steam back to liquid water so that the volatile organic compounds can be extracted. Because the boiling points of cannabinoids are much greater than that of water, volatile organic compounds, terpenes and/or thiols, the cannabinoids are retained in the Cannabis raw plant material.

In the embodiments, the variable-pressure steam extraction apparatus 100 may be a superheating steam extraction apparatus in which pressure of the system is increased to raise the temperature of the vapor and make it possible to remove less volatile organic compounds than would otherwise be extracted with a standard steam extraction apparatus. A superheating steam extraction apparatus may be particularly beneficial in removing thiols, such as 321 MBT, which have a volatility above that of the boiling point of water at 1 atmosphere. Likewise, thiols can be collected and added back to the purified product should a product be desired that has increased thiol content.

In another embodiment, removal of volatile organic compounds, including the terpenes and/or thiols, from Cannabis may be achieved by hydrodistillation. Hydrodistillation involves the complete immersion of the Cannabis raw plant material in water, followed by boiling. This method protects the essential oils extracted since the surrounding water acts as a barrier to prevent it from overheating. The steam and essential oil vapor are condensed to an aqueous fraction. The advantage of this technique is that the required material can be distilled at a temperature below 100° C., under reduced atmospheric pressure or if a solvent is used that has a low boiling point.

In conventional processes of extracting essential oils using a steam extraction apparatus, the essential oils are separated from the water based on density and the plant material is discarded. However, according to the disclosed embodiments, the desired product is the extracted plant material. After the essential oils have been extracted, the Cannabis is then dried to remove any residual water that results from the process. The result of this process is a Cannabis product from which the essential oils, including the terpenes and/or thiols, have been substantially removed and substantially all of the naturally occurring Total Potential cannabinoid content has been retained as is substantially all of the original plant structure of the plant material.

With respect to the embodiment of FIG. 1, as seen in FIG. 2, the process begins with water being placed in a boiling flask with a fitted neck (e.g., 24/40) and the boiling flask being placed into a heating mantel (S101). Cannabis raw plant material is the placed into a second glass vessel with a male fitting below and a female fitting above, and a filter or glass wool is used to plug the bottom fitting to prevent the Cannabis raw plant material from falling into the boiling flask but allowing steam to pass through the raw plant material (S102). The two flasks are then connected using a fitted angle tube and the angle tube that is connected to a water-jacked condenser (S103). Subsequently, the boiling flask is heated until the water boils (e.g., 5-30 minutes), and the steam carries the volatile organic compounds and/or essential oils from the Cannabis leaving behind substantially all of the cannabinoids in the Cannabis plant material (S104). The steam may be passed through the Cannabis raw plant material for any suitable duration of time. For example, the duration may be in the range of 1 to 120 minutes, 1 to 30 minutes, 5 to 30 minutes, or 10 to 20 minutes. The condenser empties into a beaker or a separatory funnel (S105). The Cannabis plant material is then recovered and dried (S106 and S107). The dried Cannabis plant material, then substantially devoid of volatile organic compounds and/or essential oils, represents the primarily modified Cannabis product.

With respect to the embodiment of FIG. 7, as seen in FIG. 8, the process begins with water being placed in the reservoir 102 and the Cannabis plant material being placed into the processing column 103 (S301). The reservoir 102 and the processing column 103 are connected using a silicon gasket and a vacuum pump clamp coupler 105, and cold water is connected to the condenser 104 (S302). With the pressure valve 108 in an initial open position, the reservoir 102 is heated until the water boils (˜30 minutes). The pressure valve 108 may then be adjusted and/or closed as necessary to achieve the desired pressure and temperature of the apparatus, and the steam carries the volatile organic compounds and/or essential oils from the Cannabis leaving behind the cannabinoids in the Cannabis (S303). The condenser 104 empties into the extract container 150 (S304). The cannabis plant material is recovered and dried (S305). The dried cannabis plant material, virtually devoid of volatile organic compounds and/or essential oils, represents a new Cannabis product, i.e., the primarily modified Cannabis product (S306). The dried cannabis plant material can be extracted with organic solvent to recover the cannabinoids that are without any significant contaminating volatile organic compounds and essential oils (S307). This new Cannabis product can be combined with various carbon-containing compounds to create another new cannabis product, i.e., the secondarily modified Cannabis product (S308).

In the embodiments, the essential oils may be removed using a vacuum desiccation system 20. As shown in FIG. 3, the harvested plant material is placed in a vacuum chamber 25 that is sealed, and vacuum is applied via the vacuum trap 30 and vacuum pump 35. The boiling point of any given liquid is the temperature at which the vapor pressure of the liquid equals the pressure surrounding the liquid. By reducing the pressure sufficiently, a liquid can be made to boil at room temperature. For example, in the embodiments, the boiling point of isoprene, a terpene naturally occurring in Cannabis, is lowered by 0.0382° C. per millimeter of mercury decreased from atmospheric pressure (760 mm), as described in Bekkedahl, N., Wood, L. A. & Wojciechowski, M. Some Physical Properties of Isoprene, Journal of Research of the National Bureau of Standards, 17, 883-894 (1936). Accordingly, isoprene will boil or volatilize at room temperature (25° C.) when the atmospheric pressure is reduced by 235 mm of mercury. Because the boiling point of cannabinoids is significantly higher than that of terpenes, they are retained in the Cannabis raw plant material that has been processed under reduced atmospheric pressure.

Modified Cannabis Product

A modified Cannabis product according to the disclosed embodiments is formed by extracting volatile organic compounds from Cannabis raw plant material to form a purified Cannabis product, and then adding at least one volatile organic compound such as, for example, a volatile unsaturated hydrocarbon, to the purified Cannabis product to form the modified Cannabis product, which results in an enhanced user experience during combustion and inhalation of the modified Cannabis product.

Using a primarily modified Cannabis product from which the volatile organic compounds have been extracted, removed or significantly reduced as the starting material for the further modification of the odor and flavor of the primarily modified Cannabis product by way of introducing, or adding, novel combinations of the various volatile organic compounds found in the essential oils of other plants or derivatives thereof, or synthetically produced volatile chemicals, alters the odor and flavor of the primarily modified Cannabis product to make it more desirable to Cannabis users that prefer a more acceptable odor and flavor.

The modification of the odor and flavor of Cannabis experienced when the Cannabis product is combusted and inhaled can be achieved by adding any volatile organic compound, essential oil, including the terpenes and/or thiols, naturally occurring or synthetic, in any suitable combination to the primarily modified Cannabis product from which the naturally occurring volatile organic compounds have been substantially removed or reduced to form a secondarily modified Cannabis product. In the embodiments, the volatile organic compounds include, but are not limited to, naturally occurring or synthetic terpene compounds, terpenoid compounds, essential oil compounds, ester compounds, aldehyde compounds, alcohol compounds, and mixtures and/or derivatives thereof.

The terpene compounds added may include, but are not limited to, one or more of any specific class of naturally occurring or synthetic hemiterpenes, monoterpenes, sesquiterpenes, diterpenes, sesterterpenes, triterpenes, sesquarterpenes, tetraterpenes, or polyterpenes, and mixtures or derivatives thereof, or specific terpenes including, but not limited to, isoprene, α-pinene. β-pinene, Δ3-carene, d-limonene, camphene, myrcene, β-phellandrene, sabinene, α-terpinene, ocimene, α-thujene, terpinolene, γ-terpinene, and mixtures or derivatives thereof.

The terpenoid compounds added may include, but are not limited to, one or more of any specific class of naturally occurring or synthetic terpenoids such as hemiterpenoids, monoterpenoids, sesquiterpenoids, diterpenoids, sesterterpenoids, triterpenoids, tetraterpenoids, polyterpenoid, and mixtures or derivatives thereof.

The essential oil compounds added may include, but are not limited to, one or more of any specific class of naturally occurring or synthetic cannabis, angelica, basil, bergamot, Roman chamomile, German chamomile, cinnamon bark, citrus rind, clary sage, clove, coriander, dill, eucalyptus globulus, frankincense, galbanum, geranium, ginger, grapefruit, hyssop, Idaho blue spruce, juniper, jasmine, Laurus nobilis, lavender, lemon, lemongrass, lime, lemonbalm, marjoram, myrrh, myrtle, nutmeg, orange, oregano, patchouli, pepper, peppermint, petitgrain, pine, rosemary, rose, savory, sage, sandalwood, spearmint, spruce, tarragon, tangerine, thyme, valerian, vetiver, ylang ylang, and mixtures or derivatives thereof.

In embodiments, the thiols may include, but are not limited to, 321 MBT, 4MMP, 3MH, and 3MHA. These thiols have a very strong odor and may be desirable to some consumers. The addition of thiols may also be useful in creating a reproducible product, as will be understood by one of ordinary skill in the art.

Moreover, the aldehyde compounds, ester compounds, and alcohol compounds are not specifically limited. It will be understood that any suitable aldehyde compound, ester compound, alcohol compound, other compound that provides odor and flavor of the primarily modified Cannabis product to make it more desirable to Cannabis is within the scope of this disclosure.

A method (i.e., secondary modification) for forming the modified Cannabis product is as follows. The primary modified Cannabis product, i.e., a Cannabis product from which the essential oils have been extracted, removed or significantly reduced for the purpose of modifying the odor and flavor experienced when the plant or plant material is combusted and inhaled, may then be subjected to secondary modification. With reference to FIG. 4, this process may include providing a primarily modified Cannabis product according the first embodiment (i.e., steps S201, S202, S203, S204, S205, S206 and S207). For example, the primarily modified Cannabis product may be a product formed according to the primary modification process discussed herein. Subsequently, various volatile organic compounds are added to the primarily modified Cannabis product (S208).

In the embodiments, the secondary modification process may include any combination or mixture of the above-described compounds, i.e., additive or modification “profiles.” The profiles may include specific compounds including concentrations that are known or determined to have specific scents, effects, etc. The profiles may be specified (i.e., according to a predetermined “recipe”) or unspecified according random selection. The effectiveness or user preference may recorded for future use in, e.g., ranking flavors or medicinal or therapeutic benefits.

EXAMPLES

The following examples are illustrative of the disclosed embodiments. All tests were performed using HPLC-UV. It is known that decarboxylation of THC and CBD acids occur during any smoking or cooking process, i.e., changing of the THC and CBD acids into THC and CBD. Therefore, the actual amount of THC and CBD differs from the amount of “Total Potential” THC and CBD. In the examples, the liquid chromatography analysis occurs at room temperature and does not decarboxylate any THC or CBD, thereby yielding separate values for THCa, THC, CBDa and CBD, which are then combined to derive the Total Potential THC and Total Potential CBD result using the following formulae:

Total Potential THC=THCa*0.877+Δ9-THC

Total Potential CBD=CBDa*0.877+CBD

Moreover, the following abbreviations/notes apply throughout the examples:

ND=Non Detect

LOQ=Limit of Quantitation

Cannabinoids for flower and trim reported as received.

Examples 1-3 represent three different Marijuana samples selected from the same strain. Examples 4-6 represent three different Hemp samples selected from the same strain. Example 1 (sample C-0) and Example 4 (H-0) represent the control groups and were analyzed for cannabinoid and terpene content without application of the disclosed steam extraction process. Example 2 (sample C-10) and Example 5 (H-10) were subjected to 10 minutes of the disclosed steam extraction process and then analyzed for cannabinoid and terpene content. Example 3 (sample C-20) and Example 6 (H-20) were subjected to 20 minutes of the disclosed steam extraction process and then analyzed for cannabinoid and terpene content. The results are illustrated below.

Example 1 C-0

Cannabinoids LOQ Mass Mass Analyte (%) (%) (mg/g) THCa 0.1 17.8 178 Δ9-THC 0.1 1 10 Δ8-THC 0.1 0.2 2 CBD 0.1 ND ND CBDa 0.1 0.1 1 CBC 0.1 <0.1 <1 CBG 0.1 0.1 1 CBN 0.1 ND ND THCV 0.1 ND ND CBGa 0.1 0.6 6 Total 19.7 197 Total Potential THC 16.8% Total Potential CBD  0.1%

C-0

Terpenes LOQ Mass Mass Analyte (%) (%) (mg/g) β-Caryophyllene 0.05 0.56 5.6 δ-Limonene 0.05 0.16 1.6 α-Humulene 0.05 0.14 1.4 Linalool 0.05 0.05 0.5 α-Pinene 0.02 0.2 α-Bisabolol 0.05 <0.05 <0.5 β-Myrcene 0.05 <0.05 <0.5 β-Pinene 0.05 <0.05 <0.5 Caryophyllene Oxide 0.05 <0.05 <0.5 Ocimene 0.05 ND ND Terpinolene 0.05 ND ND trans-Nerolidol 0.05 <0.05 <0.5

Example 2 C-10

Cannabinoids LOQ Mass Mass Analyte (%) (%) (mg/g) THCa 0.1 9.7 97 Δ9-THC 0.1 15.4 154 Δ8-THC 0.1 <0.1 <1 CBD 0.1 ND ND CBDa 0.1 0.1 1 CBC 0.1 0.1 1 CBG 0.1 0.2 2 CBN 0.1 0.1 1 THCV 0.1 0.1 1 CBGa 0.1 0.5 5 Total 26.2 262 Total Potential THC 24.0% Total Potential CBD  0.1%

C-10

Terpenes LOQ Mass Mass Analyte (%) (%) (mg/g) β-Caryophyllene 0.05 0.22 2.2 α-Humulene 0.05 0.07 0.7 α-Bisabolol 0.05 0.07 0.7 trans-Nerolidol 0.05 0.05 0.5 β-Myrcene 0.05 ND ND β-Pinene 0.05 ND ND Caryophyllene Oxide 0.05 <0.05 <0.5 δ-Limonene 0.05 <0.05 <0.5 Linalool 0.05 <0.05 <0.5 Ocimene 0.05 ND ND Terpinolene 0.05 ND ND α-Pinene ND ND

Example 3 C-20

Cannabinoids LOQ Mass Mass Analyte (%) (%) (mg/g) THCa 0.1 4.7 47 Δ9-THC 0.1 16.9 169 Δ8-THC 0.1 ND ND CBD 0.1 ND ND CBDa 0.1 <0.1 <1 CBC 0.1 0.1 1 CBG 0.1 0.3 3 CBN 0.1 0.1 1 THCV 0.1 0.1 1 CBGa 0.1 0.4 4 Total 22.6 226 Total Potential THC 21.1% Total Potential CBD <LOQ

C-20

Terpenes LOQ Mass Mass Analyte (%) (%) (mg/g) α-Bisabolol 0.05 0.08 0.8 β-Caryophyllene 0.05 0.05 0.5 α-Humulene 0.05 <0.05 <0.5 β-Myrcene 0.05 ND ND β-Pinene 0.05 ND ND Caryophyllene Oxide 0.05 <0.05 <0.5 δ-Limonene 0.05 ND ND Linalool 0.05 ND ND Ocimene 0.05 ND ND Terpinolene 0.05 ND ND trans-Nerolidol 0.05 <0.05 <0.5 α-Pinene ND ND

Example 4 H-0

Cannabinoids LOQ Mass Mass Analyte (%) (%) (mg/g) THCa 0.1 0.4 4 Δ9-THC 0.1 ND ND Δ8-THC 0.1 ND ND CBD 0.1 0.1 1 CBDa 0.1 10.5 105 CBC 0.1 <0.1 <1 CBG 0.1 <0.1 <1 CBN 0.1 ND ND THCV 0.1 ND ND CBGa 0.1 0.9 9 Total 11.9 119 Total Potential THC 0.4% Total Potential CBD 9.3%

H-0

Terpenes LOQ Mass Mass Analyte (%) (%) (mg/g) β-Myrcene 0.05 0.61 6.1 β-Caryophyllene 0.05 0.48 4.8 α-Humulene 0.05 0.15 1.5 α-Pinene 0.13 1.3 Ocimene 0.05 0.06 0.6 α-Bisabolol 0.05 <0.05 <0.5 β-Pinene 0.05 <0.05 <0.5 Caryophyllene Oxide 0.05 <0.05 <0.5 δ-Limonene 0.05 <0.05 <0.5 Linalool 0.05 <0.05 <0.5 Terpinolene 0.05 ND ND trans-Nerolidol 0.05 <0.05 <0

Example 5 H-10

Cannabinoids LOQ Mass Mass Analyte (%) (%) (mg/g) THCa 0.1 0.1 1 Δ9-THC 0.1 0.4 4 Δ8-THC 0.1 ND ND CBD 0.1 5.2 52 CBDa 0.1 4.6 46 CBC 0.1 0.7 7 CBG 0.1 0.2 2 CBN 0.1 ND ND THCV 0.1 ND ND CBGa 0.1 0.3 3 Total 11.5 115 CBGa 0.1 0.3 3 Total 11.5 11.5 Total Potential THC 0.4% Total Potential CBD 9.3%

H-10

Terpenes LOQ Mass Mass Analyte (%) (%) (mg/g) β-Caryophyllene 0.05 0.05 0.5 α-Bisabolol 0.05 <0.05 <0.5 α-Humulene 0.05 <0.05 <0.5 β-Myrcene 0.05 ND ND β-Pinene 0.05 ND ND Caryophyllene Oxide 0.05 <0.05 <0.5 δ-Limonene 0.05 ND ND Linalool 0.05 ND ND Ocimene 0.05 ND ND Terpinolene 0.05 ND ND trans-Nerolidol 0.05 <0.05 <0.5 α-Pinene ND ND

Example 6 H-20

Cannabinoids LOQ Mass Mass Analyte (%) (%) (mg/g) THCa 0.1 <0.1 <1 Δ9-THC 0.1 0.3 3 Δ8-THC 0.1 ND ND CBD 0.1 4.9 49 CBDa 0.1 1.5 15 CBC 0.1 0.5 5 CBG 0.1 0.3 3 CBN 0.1 ND ND THCV 0.1 ND ND CBGa 0.1 0.2 2 Total 7.6 76 Total Potential THC 0.3% Total Potential CBD 6.2%

H-20

Terpenes LOQ Mass Mass Analyte (%) (%) (mg/g) α-Bisabolol 0.05 <0.05 <0.5 α-Humulene 0.05 <0.05 <0.5 β-Caryophyllene 0.05 <0.05 <0.5 β-Myrcene 0.05 ND ND β-Pinene 0.05 ND ND Caryophyllene Oxide 0.05 <0.05 <0.5 δ-Limonene 0.05 ND ND Linalool 0.05 ND ND Ocimene 0.05 ND ND Terpinolene 0.05 ND ND trans-Nerolidol 0.05 <0.05 <0.5 α-Pinene ND ND

The results of the cannabinoid content analysis of the Marijuana samples in Examples 1, 2 and 3 are illustrated in graphical format in FIGS. 5A, 5C and 5E, respectively. The results of the terpene content analysis of the Marijuana samples in Examples 1, 2 and 3 are illustrated in graphical format in FIGS. 5B, 5D and 5F, respectively. The results of the cannabinoid content analysis of the Hemp samples in Examples 4, 5 and 6 are illustrated in graphical format in FIGS. 6A, 6C and 6E, respectively. The results of the terpene content analysis of the Hemp samples in Examples 4, 5 and 6 are illustrated in graphical format in FIGS. 6B, 6D and 6F, respectively.

In comparing Examples 1, 2 and 3 (C-0, C-10 and C-20), it is evident that the terpene content drops precipitously from the control sample (Example 1) to Example 2 that was subjected to the disclosed steam extraction process for 10 minutes. The terpene content further drops from Example 2 to Example 3 that was subjected to the disclosed steam extraction process for an additional 10 minutes (20 minutes in total). Thus, the disclosed primary modification process provides clear advantages in terms of removing terpene content from Marijuana. It is also apparent that increased exposure to the disclosed process at least up to 20 minutes increases the effectiveness of the terpene removal.

Moreover, the Total Potential THC content does not decrease from Example 1 (16.8%) to Example 2 (24.0%) and does not significantly decrease from Example 2 (24.0%) to Example 3 (21.1%). While the Total Potential THC content varies somewhat across Examples 1-3, this believed to be a result of natural variability from one flower to another in the sample. The disclosed processes do not increase the potential THC. The starting potential cannabinoids (THCa+THC) should not change, only the ratio should change, as the acid is decarboxylated and converted to the non-acid form. In this regard, the Marijuana samples (C-0, C-10 and C-20) were all selected from the following sample strain:

As seen in the figure above, the reported amount of THC for the sample strain was actually 28%. None of the flowers selected for C-0, C-10 and C-20 assayed at this level, but Example 2 (24.0%) to Example 3 (21.1%) are closer to the dispensary's reported value of 28%. It is also worth noting that the average of the values in Examples 1 and 2 is about the value in Example 3. Therefore, the data clearly show that the disclosed primary modification process selectively extracts the terpenes from Marijuana while retaining substantially all of the THC potential.

In the Hemp samples, the trend is more stable. In comparing Examples 4, 5 and 6 (H-0, H-10 and H-20), it is evident that the terpene content drops precipitously from the control sample (Example 4) to Examples 5 and 6 that were subjected to the disclosed steam extraction process for 10 and 20 minutes, respectively. Thus, the disclosed primary modification process provides clear advantages in terms of removing terpene content from Hemp. Further, the Total Potential CBD content stays the same from Example 4 (9.3%) to Example 5 (9.3%) and does not significantly decrease from Example 5 (9.3%) to Example 6 (6.2%). The important point is that the potential cannabinoids are largely retained but the terpenes show a 10-fold reduction. Therefore, the data clearly show that the disclosed primary modification process selectively extracts the terpenes from Hemp while retaining substantially all of the CBD potential.

Examples 7-22 below exhibit Hemp samples processed using a variable-pressure steam extraction system according to embodiments.

Example 7 Hawaiian Haze

Cannabinoids LOQ Result Result Analyte % % mg/g THCa 0.05 0.32 3.2 Δ9-THC 0.05 0.29 2.9 Δ8-THC 0.05 <LOQ <LOQ CBD 0.05 3.83 38.3 CBDa 0.05 13.92 139.2 CBC 0.05 0.21 2.1 CBG 0.05 <LOQ <LOQ CBN 0.05 <LOQ <LOQ THCV 0.05 <LOQ <LOQ CBGa 0.05 0.25 2.5 Total 18.84 188.4 Total Potential THC 0.58% Total Potential CBD 16.04%

Terpenes LOQ Result Result Analyte % % mg/g α-Bisabolol 0.05 0.21 2.1 α-Pinene 0.05 0.14 1.4 β-Mycrene 0.05 0.12 1.2 β-Caryophyllene 0.05 0.07 0.7 α-Humulene 0.05 <0.05 <0.5 β-Pinene 0.05 <0.05 <0.5 Caryophyllene Oxide 0.05 <0.05 <0.5 δ-Limonene 0.05 <0.05 <0.5 Linalool 0.05 <0.05 <0.5 Ocimene 0.05 <0.05 <0.5 Terpinolene 0.05 ND ND trans-Nerolidol 0.05 <0.05 <0.5

Example 8 Hawaiian Haze Extracted

Cannabinoids LOQ Result Result Analyte % % mg/g THCa 0.05 ND ND Δ9-THC 0.05 0.47 4.7 Δ8-THC 0.05 <LOQ <LOQ CBD 0.05 9.44 94.4 CBDa 0.05 3.82 38.2 CBC 0.05 0.45 4.5 CBG 0.05 <LOQ <LOQ CBN 0.05 <LOQ <LOQ THCV 0.05 <LOQ <LOQ CBGa 0.05 <LOQ <LOQ Total 14.18 141.8 Potential THC  0.47% Potential CBD 12.79%

Terpenes LOQ Result Result Analyte % % mg/g α-Bisabolol 0.05 0.11 1.1 α-Humulene 0.05 <0.05 <0.5 α-Pinene 0.05 ND ND β-Caryophyllene 0.05 <0.05 <0.5 β-Myrcene 0.05 ND ND β-Pinene 0.05 ND ND Caryophyllene Oxide 0.05 <0.05 <0.5 δ-Limonene 0.05 ND ND Linalool 0.05 ND ND Ocimene 0.05 ND ND Terpinolene 0.05 ND ND trans-Nerolidol 0.05 <0.05 <0.5

Example 9 Strawberry Gelato

Cannabinoids LOQ Result Result Analyte % % mg/g THCa 0.05 0.21 2.1 Δ9-THC 0.05 0.33 3.3 Δ8-THC 0.05 <LOQ <LOQ CBD 0.05 4.40 44.0 CBDa 0.05 12.68 126.8 CBC 0.05 0.29 2.9 CBG 0.05 <LOQ <LOQ CBN 0.05 <LOQ <LOQ THCV 0.05 <LOQ <LOQ CBGa 0.05 0.40 4.0 Total 18.30 183.0 Total Potential THC  0.51% Total Potential CBD 15.51%

Terpenes LOQ Result Result Analyte % % mg/g α-Bisabolol 0.05 0.14 1.4 β-Caryophyllene 0.05 0.13 1.3 β-Myrcene 0.05 0.06 0.6 α-Humulene 0.05 0.05 0.5 α-Pinene 0.05 <0.05 <0.5 β-Pinene 0.05 <0.05 <0.5 Caryophyllene Oxide 0.05 <0.05 <0.5 δ-Limonene 0.05 <0.05 <0.5 Linalool 0.05 <0.05 <0.5 Ocimene 0.05 <0.05 <0.5 Terpinolene 0.05 ND ND trans-Nerolidol 0.05 <0.05 <0.5

Example 10 Strawberry Gelato Extracted

Cannabinoids LOQ Result Result Analyte % % mg/g THCa 0.05 0.18 1.8 Δ9-THC 0.05 0.44 4.4 Δ8-THC 0.05 <LOQ <LOQ CBD 0.05 7.73 77.3 CBDa 0.05 6.94 69.4 CBC 0.05 0.44 4.4 CBG 0.05 0.15 1.5 CBN 0.05 <LOQ <LOQ THCV 0.05 <LOQ <LOQ CBGa 0.05 0.15 1.5 Total 16.03 160.3 Total Potential THC 0.59% Total Potential CBD 13.82%

Terpenes LOQ Result Result Analyte % % mg/g α-Bisabolol 0.05 0.13 1.3 α-Humulene 0.05 <0.05 <0.5 α-Pinene 0.05 ND ND β-Caryophyllene 0.05 <0.05 <0.5 β-Myrcene 0.05 ND ND β-Pinene 0.05 ND ND Caryophyllene Oxide 0.05 <0.05 <0.5 δ-Limonene 0.05 ND ND Linalool 0.05 ND ND Ocimene 0.05 <0.05 <0.5 Terpinolene 0.05 ND ND trans-Nerolidol 0.05 <0.05 <0.5

Example 11 Blue Gelato

Cannabinoids LOQ Result Result Analyte % % mg/g THCa 0.05 0.23 2.3 Δ9-THC 0.05 0.30 3.0 Δ8-THC 0.05 <LOQ <LOQ CBD 0.05 3.80 38.0 CBDa 0.05 12.54 125.4 CBC 0.05 0.33 3.3 CBG 0.05 <LOQ <LOQ CBN 0.05 <LOQ <LOQ THCV 0.05 <LOQ <LOQ CBGa 0.05 1.75 17.5 Total 18.93 189.3 Total Potential THC 0.49% Total Potential CBD 14.79%

Terpenes LOQ Result Result Analyte % % mg/g α-Bisabolol 0.05 0.17 1.7 β-Caryophyllene 0.05 0.11 1.1 α-Humulene 0.05 <0.05 <0.5 α-Pinene 0.05 <0.05 <0.5 β-Myrcene 0.05 <0.05 <0.5 β-Pinene 0.05 <0.05 <0.5 Caryophyllene Oxide 0.05 <0.05 <0.5 δ-Limonene 0.05 <0.05 <0.5 Linalool 0.05 <0.05 <0.5 Ocimene 0.05 <0.05 <0.5 Terpinolene 0.05 ND ND trans-Nerolidol 0.05 <0.05 <0.5

Example 12 Blue Gelato Extracted

Cannabinoids LOQ Result Result Analyte % % mg/g THCa 0.05 <LOQ <LOQ Δ9-THC 0.05  0.50  5.0 Δ8-THC 0.05 <LOQ <LOQ CBD 0.05  9.77 97.7 CBDa 0.05  8.70 87.0 CBC 0.05  0.56  5.6 CBG 0.05  0.13  1.3 CBN 0.05 <LOQ <LOQ THCV 0.05 <LOQ <LOQ CBGa 0.05  0.17  1.7 Total 19.84 198.4  Total Potential THC 0.50% Total Potential CBD 17.40%

Terpenes LOQ Result Result Analyte % % mg/g α-Bisabolol 0.05  0.13  1.3 α-Humulene 0.05 <0.05 <0.5 α-Pinene 0.05 ND ND β-Caryophyllene 0.05 <0.05 <0.5 β-Myrcene 0.05 ND ND β-Pinene 0.05 ND ND Caryophyllene Oxide 0.05 <0.05 <0.5 δ-Limonene 0.05 ND ND Linalool 0.05 ND ND Ocimene 0.05 ND ND Terpinolene 0.05 ND ND trans-Nerolidol 0.05 <0.05 <0.5

Example 13 NY CBDiesel

Cannabinoids LOQ Result Result Analyte % % mg/g THCa 0.05 0.25 2.5 Δ9-THC 0.05 0.27 2.7 Δ8-THC 0.05 <LOQ <LOQ CBD 0.05 3.13 31.3  CBDa 0.05 11.58  115.8  CBC 0.05 0.19 1.9 CBG 0.05 <LOQ <LOQ CBN 0.05 <LOQ <LOQ THCV 0.05 <LOQ <LOQ CBGa 0.05 0.40 4.0 Total 15.81  158.1  Total Potential THC 0.48% Total Potential CBD 13.29%

Terpenes LOQ Result Result Analyte % % mg/g β-Myrcene 0.05 0.14 1.4 α-Pinene 0.05 0.09 0.9 α-Bisabolol 0.05 0.06 0.6 α-Humulene 0.05 <0.05 <0.5 β-Caryophyllene 0.05 <0.05 <0.5 β-Pinene 0.05 <0.05 <0.5 Caryophyllene Oxide 0.05 <0.05 <0.5 δ-Limonene 0.05 <0.05 <0.5 Linalool 0.05 <0.05 <0.5 Ocimene 0.05 <0.05 <0.5 Terpinolene 0.05 ND ND trans-Nerolidol 0.05 <0.05 <0.5

Example 14 NY CBDiesel Extracted

Cannabinoids LOQ Result Result Analyte % % mg/g THCa 0.05 <LOQ <LOQ Δ9-THC 0.05  0.44  4.4 Δ8-THC 0.05 <LOQ <LOQ CBD 0.05  7.09 70.9 CBDa 0.05  6.50 65.0 CBC 0.05  0.31  3.1 CBG 0.05  0.21  2.1 CBN 0.05 <LOQ <LOQ THCV 0.05 <LOQ <LOQ CBGa 0.05  0.20  2.0 Total 14.75 147.5  Total Potential THC 0.44% Total Potential CBD 12.79%

Terpenes LOQ Result Result Analyte % % mg/g α-Bisabolol 0.05 <0.05 <0.5 α-Humulene 0.05 <0.05 <0.5 α-Pinene 0.05 ND ND β-Caryophyllene 0.05 <0.05 <0.5 β-Myrcene 0.05 ND ND β-Pinene 0.05 ND ND Caryophyllene Oxide 0.05 <0.05 <0.5 δ-Limonene 0.05 ND ND Linalool 0.05 ND ND Ocimene 0.05 ND ND Terpinolene 0.05 ND ND trans-Nerolidol 0.05 <0.05 <0.5

Example 15 T1

Cannabinoids LOQ Result Result Analyte % % mg/g THCa 0.05  0.18  1.8 Δ9-THC 0.05  0.34  3.4 Δ8-THC 0.05 <LOQ <LOQ CBD 0.05  5.01 50.1 CBDa 0.05 11.80 118.1  CBC 0.05  0.37  3.7 CBG 0.05 <LOQ <LOQ CBN 0.05 <LOQ <LOQ THCV 0.05 <LOQ <LOQ CBGa 0.05  0.13  1.3 Total 17.84 178.4  Total Potential THC 0.50% Total Potential CBD 15.36%

Terpenes LOQ Result Result Analyte % % mg/g β-Caryophyllene 0.05 0.17 1.7 α-Bisabolol 0.05 0.16 1.6 α-Humulene 0.05 0.05 0.5 α-Pinene 0.05 <0.05 <0.5 β-Myrcene 0.05 <0.05 <0.5 β-Pinene 0.05 <0.05 <0.5 Caryophyllene Oxide 0.05 <0.05 <0.5 δ-Limonene 0.05 <0.05 <0.5 Linalool 0.05 <0.05 <0.5 Ocimene 0.05 <0.05 <0.5 Terpinolene 0.05 ND ND trans-Nerolidol 0.05 <0.05 <0.5

Example 16 T1 Extracted

Cannabinoids LOQ Result Result Analyte % % mg/g THCa 0.05 ND ND Δ9-THC 0.05  0.40  4.0 Δ8-THC 0.05 <LOQ <LOQ CBD 0.05  7.73 77.3 CBDa 0.05  5.74 57.4 CBC 0.05  0.48  4.8 CBG 0.05 <LOQ <LOQ CBN 0.05 <LOQ <LOQ THCV 0.05 <LOQ <LOQ CBGa 0.05 <LOQ <LOQ Total 14.35 143.5  Total Potential THC 0.40% Total Potential CBD 12.76%

Terpenes LOQ Result Result Analyte % % mg/g α-Bisabolol 0.05  0.15  1.5 β-Caryophyllene 0.05  0.05  0.5 α-Humulene 0.05 <0.05 <0.5 α-Pinene 0.05 ND ND β-Myrcene 0.05 ND ND β-Pinene 0.05 ND ND Caryophyllene Oxide 0.05 <0.05 <0.5 δ-Limonene 0.05 ND ND Linalool 0.05 <0.05 <0.5 Ocimene 0.05 <0.05 <0.5 Terpinolene 0.05 ND ND trans-Nerolidol 0.05 <0.05 <0.5

Example 17 Legendary OG

Cannabinoids LOQ Result Result Analyte % % mg/g THCa 0.05 0.15 1.5 Δ9-THC 0.05 0.37 3.7 Δ8-THC 0.05 <LOQ <LOQ CBD 0.05 5.26 52.6 CBDa 0.05 10.42 104.2 CBC 0.05 0.25 2.5 CBG 0.05 0.24 2.4 CBN 0.05 <LOQ <LOQ THCV 0.05 <LOQ <LOQ CBGa 0.05 0.38 3.8 Total 17.06 170.6 Total Potential THC  0.50% Total Potential CBD 14.40%

Terpenes LOQ Result Result Analyte % % mg/g β-Caryophyllene 0.05 0.35 3.5 α-Humulene 0.05 0.14 1.4 α-Bisabolol 0.05 0.10 1.0 Linalool 0.05 0.07 0.7 δ-Limonene 0.05 0.06 0.6 Caryophyllene Oxide 0.05 0.05 0.5 α-Pinene 0.05 <0.05 <0.5 β-Myrcene 0.05 ND ND β-Pinene 0.05 <0.05 <0.5 Ocimene 0.05 <0.05 <0.5 Terpinolene 0.05 ND ND trans-Nerolidol 0.05 <0.05 <0.5

Example 18 Legendary OG Extracted

Cannabinoids LOQ Result Result Analyte % % mg/g THCa 0.05 <LOQ <LOQ Δ9-THC 0.05  0.35  3.5 Δ8-THC 0.05 <LOQ <LOQ CBD 0.05  6.99 69.9 CBDa 0.05  4.84 48.4 CBC 0.05  0.29  2.9 CBG 0.05  0.18  1.8 CBN 0.05 <LOQ <LOQ THCV 0.05 <LOQ <LOQ CBGa 0.05  0.09  0.9 Total 12.74 127.4  Total Potential THC 0.35% Total Potential CBD 11.24%

Terpenes LOQ Result Result Analyte % % mg/g α-Bisabolol 0.05 0.06 0.6 α-Humulene 0.05 <0.05 <0.5 α-Pinene 0.05 ND ND β-Caryophyllene 0.05 <0.05 <0.5 β-Myrcene 0.05 ND ND β-Pinene 0.05 ND ND Caryophyllene Oxide 0.05 <0.05 <0.5 δ-Limonene 0.05 ND ND Linalool 0.05 ND ND Ocimene 0.05 ND ND Terpinolene 0.05 ND ND trans-Nerolidol 0.05 <0.05 <0.5

Example 19 Special Sauce

Cannabinoids LOQ Result Result Analyte % % mg/g THCa 0.05  0.13  1.3 Δ9-THC 0.05  0.46  4.6 Δ8-THC 0.05 <LOQ <LOQ CBD 0.05  6.34 63.4 CBDa 0.05 11.25 112.5  CBC 0.05  0.37  3.7 CBG 0.05  0.18  1.8 CBN 0.05 <LOQ <LOQ THCV 0.05 <LOQ <LOQ CBGa 0.05  0.27  2.7 Total 19.01 190.1  Total Potential THC 0.58% Total Potential CBD 16.20%

Terpenes LOQ Result Result Analyte % % mg/g α-Bisabolol 0.05  0.27  2.7 β-Caryophyllene 0.05  0.14  1.4 β-Myrcene 0.05  0.13  1.3 α-Pinene 0.05  0.09  0.9 α-Humulene 0.05 <0.05 <0.5 β-Pinene 0.05 <0.05 <0.5 Caryophyllene Oxide 0.05 <0.05 <0.5 δ-Limonene 0.05 <0.05 <0.5 Linalool 0.05 <0.05 <0.5 Ocimene 0.05 <0.05 <0.5 Terpinolene 0.05 ND ND trans-Nerolidol 0.05 <0.05 <0.5

Example 20 Special Sauce Extracted

Cannabinoids LOQ Result Result Analyte % % mg/g THCa 0.05 <LOQ <LOQ Δ9-THC 0.05  0.46  4.6 Δ8-THC 0.05 <LOQ <LOQ CBD 0.05  8.44 84.4 CBDa 0.05  5.36 53.6 CBC 0.05  0.44  4.4 CBG 0.05  0.22  2.2 CBN 0.05 <LOQ <LOQ THCV 0.05 <LOQ <LOQ CBGa 0.05  0.13  1.3 Total 15.05 150.5  Total Potential THC 0.46% Total Potential CBD 13.13%

Terpenes LOQ Result Result Analyte % % mg/g α-Bisabolol 0.05  0.18  1.8 α-Humulene 0.05 <0.05 <0.5 α-Pinene 0.05 ND ND β-Caryophyllene 0.05 <0.05 <0.5 β-Myrcene 0.05 ND ND β-Pinene 0.05 ND ND Caryophyllene Oxide 0.05 <0.05 <0.5 δ-Limonene 0.05 ND ND Linalool 0.05 ND ND Ocimene 0.05 ND ND Terpinolene 0.05 ND ND trans-Nerolidol 0.05 <0.05 <0.5

Example 21 Doctor Wu

Cannabinoids LOQ Result Result Analyte % % mg/g THCa 0.05 0.15 1.5 Δ9-THC 0.05 0.35 3.5 Δ8-THC 0.05 <LOQ <LOQ CBD 0.05 4.27 42.7 CBDa 0.05 8.93 89.3 CBC 0.05 0.28 2.8 CBG 0.05 0.18 1.8 CBN 0.05 <LOQ <LOQ THCV 0.05 <LOQ <LOQ CBGa 0.05 0.32 3.2 Total 14.47 144.7 Potential THC  0.48% Potential CBD 12.10%

Terpenes LOQ Result Result Analyte % % mg/g α-Bisabolol 0.05 0.06 0.6 α-Humulene 0.05 <0.05 <0.5 α-Pinene 0.05 <0.05 <0.5 β-Caryophyllene 0.05 <0.05 <0.5 β-Myrcene 0.05 <0.05 <0.5 β-Pinene 0.05 <0.05 <0.5 Caryophyllene Oxide 0.05 <0.05 <0.5 δ-Limonene 0.05 <0.05 <0.5 Linalool 0.05 <0.05 <0.5 Ocimene 0.05 ND ND Terpinolene 0.05 ND ND trans-Nerolidol 0.05 <0.05 <0.5

Example 22 Doctor Wu Extracted

Cannabinoids LOQ Result Result Analyte % % mg/g THCa 0.05 <LOQ <LOQ Δ9-THC 0.05  0.55  5.5 Δ8-THC 0.05 <LOQ <LOQ CBD 0.05  9.15 91.5 CBDa 0.05  4.86 48.6 CBC 0.05  0.49  4.9 CBG 0.05  0.30  3.0 CBN 0.05 <LOQ <LOQ THCV 0.05 <LOQ <LOQ CBGa 0.05  0.15  1.5 Total 15.50 155.0  Total Potential THC 0.55% Total Potential CBD 13.41%

Terpenes LOQ Result Result Analyte % % mg/g α-Bisabolol 0.05  0.07  0.7 α-Humulene 0.05 ND ND α-Pinene 0.05 ND ND β-Caryophyllene 0.05 <0.05 <0.5 β-Myrcene 0.05 ND ND β-Pinene 0.05 ND ND Caryophyllene Oxide 0.05 <0.05 <0.5 δ-Limonene 0.05 ND ND Linalool 0.05 ND ND Ocimene 0.05 ND ND Terpinolene 0.05 ND ND trans-Nerolidol 0.05 <0.05 <0.5

The Table below summarizes the terpene content of the above Examples 7-22.

Caryophyl- a- b- b- a- b- a- d- lene Trans- Terpino- Strain Bisabolol Caryophyllene Myrcene Pinene Pinene Humulene Linalool Limonene Oxide Ocimene Nerolidol lene Special 2.7 1.4 1.3 0.9 <0.5 <0.5 <0.5 <0.5 <0.5 <0.5 <0.5 ND Sauce Special 1.8 <0.5 ND ND ND <0.5 ND ND <0.5 ND <0.5 ND Sauce Extracted Legendary 1 3.5 ND <0.5 <0.5 1.4 0.7 0.6 0.5 <0.5 <0.5 ND OG Legendary 0.6 <0.5 ND ND ND <0.5 ND ND <0.5 ND <0.5 ND OG Extracted T1 1.6 1.7 <0.5 <0.5 <0.5 0.5 <0.5 <0.5 <0.5 <0.5 <0.5 ND T1 1.5 0.5 ND ND ND <0.5 <0.5 ND <0.5 <0.5 <0.5 ND Extracted NY 0.6 <0.5 1.4 0.9 <0.5 <0.5 <0.5 <0.5 <0.5 <0.5 <0.5 ND CBDiesel NY <0.5 <0.5 ND ND <0.5 <0.5 ND ND <0.5 ND <0.5 ND CBDiesel Extracted Blue 1.7 1.1 <0.5 <0.5 <0.5 <0.5 <0.5 <0.5 <0.5 <0.5 <0.5 ND Gelato Blue 1.3 <0.5 ND ND ND <0.5 ND ND <0.5 ND <0.5 ND Gelato Extracted Hawaiian 2.1 0.7 1.2 1.4 <0.5 <0.5 <0.5 <0.5 <0.5 <0.5 <0.5 ND Haze Hawaiian 1.1 <0.5 ND ND ND <0.5 ND ND <0.5 ND <0.5 ND Haze Extracted Strawberry 1.4 1.3 0.6 <0.5 <0.5 0.5 <0.5 <0.5 <0.5 <0.5 <0.5 ND Gelato Strawberry 1.3 <0.5 ND ND ND <0.5 ND ND <0.5 <0.5 <0.5 ND Gelato Extracted Dr Wu 0.6 <0.5 <0.5 <0.5 <0.5 <0.5 <0.5 <0.5 <0.5 ND <0.5 ND Dr Wu 0.7 <0.5 ND ND ND ND ND ND <0.5 ND <0.5 ND Extracted

The results of the cannabinoid content analysis of the Marijuana samples in Examples 7-22 are illustrated in graphical format in FIGS. 9A, 10A, 11A, 12A, 13A, 14A, 15A, 16A, 17A, 18A, 19A, 20A, 21A, 22A, 23A, and 24A, respectively. The results of the terpene content analysis of the Marijuana samples in Examples 7-22 are illustrated in graphical format in FIGS. 9B, 10B, 11B, 12B, 13B, 14B, 15B, 16B, 17B, 18B, 19B, 20B, 21B, 22B, 23B, and 24B, respectively.

As seen in Examples 7-22, selective extraction of different terpenes can be achieved by the choice of starting materials. Because the extraction method removes larger terpenes or those with electronegative functional groups, such as alcohol, carbonyl, or thiol groups less efficiently than lighter terpenes or those without functional groups, the choice of starting materials can be leveraged in order to make custom products with non-classical cannabis smell. For example, the sesquiterpenoid terpene alcohol, alpha-bisabolol, which has a weak sweet floral aroma of chamomile and is also reported to have anti-irritant, anti-inflammatory, and anti-microbial properties, can be selectively included in the final product by choosing a starting material that has a high content of this terpene. Alternatively, the low odor or odorless cannabis can be produced at a lower temperature or pressure by selecting a starting material that has little or no alpha-bisabolol. Therefore, both the smell and potential medicinal properties can be modified by judicious choice of starting materials.

It will be appreciated that the above-disclosed features and functions, or alternatives thereof, may be desirably combined into different compositions, systems or methods. Also, various alternatives, modifications, variations or improvements may be subsequently made by those skilled in the art. As such, various changes may be made without departing from the spirit and scope of this disclosure. 

What is claimed is:
 1. A method of modifying a naturally occurring Cannabis raw plant material, the method comprising: selectively extracting at least some volatile organic compounds from a naturally occurring Cannabis raw plant material, wherein at least some of a naturally occurring potential cannabinoid content in the Cannabis raw plant material is retained after removal of the at least some of the volatile organic compounds.
 2. The method of modifying a naturally occurring Cannabis raw plant material according to claim 1, wherein the at least some volatile organic compounds are selectively extracted by controlling a pressure in a variable-pressure steam extraction apparatus.
 3. The method of modifying a naturally occurring Cannabis raw plant material according to claim 2, wherein reducing the pressure decreases the boiling point of the at least some volatile organic compounds in the variable-pressure steam extraction apparatus.
 4. The method of modifying a naturally occurring Cannabis raw plant material according to claim 2, wherein increasing the pressure increases the boiling point of the at least some volatile organic compounds in the variable-pressure steam extraction apparatus.
 5. The method of modifying a naturally occurring Cannabis raw plant material according to claim 2, wherein the pressure in the variable-pressure steam extraction apparatus is set to be in a range of 0.0001 to 100 bar.
 6. The method of modifying a naturally occurring Cannabis raw plant material according to claim 2, wherein the pressure in the variable-pressure steam extraction apparatus is set to be in a range of 0.001 to 15 bar.
 7. The method of modifying a naturally occurring Cannabis raw plant material according to claim 2, wherein the pressure in the variable-pressure steam extraction apparatus is set to be in a range of 0.001 to 0.99 bar.
 8. The method of modifying a naturally occurring Cannabis raw plant material according to claim 2, wherein the variable-pressure steam extraction apparatus is a superheating steam extraction apparatus.
 9. The method of modifying a naturally occurring Cannabis raw plant material according to claim 1, further comprising recovering and drying the Cannabis raw plant material after removal of the at least some volatile organic compounds to form a purified Cannabis product.
 10. The method of modifying a naturally occurring Cannabis raw plant material according to claim 9, further comprising adding at least one volatile organic compound to the purified Cannabis product to form a modified Cannabis product.
 11. The method of modifying a naturally occurring Cannabis raw plant material according to claim 1, wherein the at least some volatile organic compounds are selectively extracted by hydrodistillation.
 12. The method of modifying a naturally occurring Cannabis raw plant material according to claim 1, wherein the at least some volatile organic compounds are selectively extracted by genetically modifying the naturally occurring Cannabis raw plant material.
 13. The method of modifying a naturally occurring Cannabis raw plant material according to claim 1, wherein the at least some volatile organic compounds are selectively extracted by selectively breeding the naturally occurring Cannabis raw plant material.
 14. The method of modifying a naturally occurring Cannabis raw plant material according to claim 1, wherein the at least some volatile organic compounds include an unsaturated hydrocarbon.
 15. The method of modifying a naturally occurring Cannabis raw plant material according to claim 1, wherein the at least some volatile organic compounds include a saturated hydrocarbon.
 16. The method of modifying a naturally occurring Cannabis raw plant material according to claim 1, wherein the at least some volatile organic compounds includes at least one thiol compound.
 17. The method of modifying a naturally occurring Cannabis raw plant material according to claim 16, wherein the at least one thiol compound is at least one compound selected from the group consisting of 321 MBT, 4MMP, 3MH, and 3MHA.
 18. The method of modifying a naturally occurring Cannabis raw plant material according to claim 17, wherein the at least one thiol compound is 321 MBT.
 19. The method of modifying a naturally occurring Cannabis raw plant material according to claim 1, wherein at least some of a naturally occurring physical structure in the Cannabis raw plant material is retained after removal of the at least some of the volatile organic compounds.
 20. The method of modifying a naturally occurring Cannabis raw plant material according to claim 1, wherein the at least some of the naturally occurring potential cannabinoid content in the Cannabis raw plant material is retained such that the purified Cannabis product can be at least one of (i) consumed, (ii) ingested, and (iii) combusted and inhaled, in a manner similar to the naturally occurring Cannabis raw plant material under similar conditions.
 21. A purified Cannabis product from a naturally occurring Cannabis raw plant material, the purified Cannabis product comprising: cannabinoids; and a reduced amount of volatile organic compounds relative to the Cannabis raw plant material, wherein at least one thiol compound has been removed from the Cannabis raw plant material to form the purified Cannabis product, and at least some of a naturally occurring potential cannabinoid content in the Cannabis raw plant material is retained in the purified Cannabis product after removal of the at least one thiol compound.
 22. A modified Cannabis product from a naturally occurring Cannabis raw plant material, the modified Cannabis product comprising: cannabinoids; and at least one volatile organic compound, wherein at least some volatile organic compounds have been removed from the Cannabis raw plant material to form a purified Cannabis product, at least one volatile organic compound has been added to the purified Cannabis product to form the modified Cannabis product, and at least some of a naturally occurring cannabinoid content of the Cannabis raw plant material is retained in the purified Cannabis product after removal of the at least one thiol compound.
 23. A method of extracting at least some volatile organic compounds from a naturally occurring Cannabis raw plant material, the method comprising: adjusting a pressure of a variable-pressure steam extraction apparatus based on a boiling point of at least one volatile organic compound in the naturally occurring Cannabis raw plant material; and selectively extracting the at least some volatile organic compounds from the naturally occurring Cannabis raw plant material in the variable-pressure steam extraction apparatus by operating the variable-pressure steam extraction apparatus at the pressure.
 24. The method of extracting at least one volatile organic compound according to claim 23, wherein reducing the pressure decreases the boiling point of the at least some volatile organic compounds in the variable-pressure steam extraction apparatus.
 25. The method of extracting at least one volatile organic compound according to claim 23, wherein increasing the pressure increases the boiling point of the at least some volatile organic compounds in the variable-pressure steam extraction apparatus.
 26. The method of extracting at least one volatile organic compound according to claim 23, wherein the pressure in the variable-pressure steam extraction apparatus is adjusted to be in a range of 0.0001 to 100 bar.
 27. The method of extracting at least one volatile organic compound according to claim 23, wherein the pressure in the variable-pressure steam extraction apparatus is adjusted to be in a range of 0.001 to 15 bar.
 28. The method of extracting at least one volatile organic compound according to claim 23, wherein the pressure in the variable-pressure steam extraction apparatus is adjusted to be in a range of 0.001 to 0.99 bar. 